I’m selling a 3-flat on north side of Chicago (that was making about $1300/month) and looking to 1031 into 2-3 properties that will generate cash flow of at least $3k+ month. So cash flow is my main focus. And I’ve got a demanding day job and three kids, so can’t manage a large renovation myself right now.

I want to stay in Chicagoland. And the best cash flow opportunities seem to be in the south side of Chicago. I’m looking at a 7-unit in the Jackson Park / South Shore neighborhood that is turn-key. Everything is new and it’s stabilized with 4-section 8 tenants, 3-market tenants. Group that did all the work would stay on and manage for 5%. This deal would make about $2k/month and use 60% of my exchange proceeds.

This would be our first experience with the section 8 process. But with management in place, it’s less scary. And I’m intrigued that the group that did the work to renovate would stay on and manage. Tells me they stand behind what they’re doing.

I’m anxious to hear other people’s thoughts, opinions and lessons learned on investing in the south side of chicago. Also, curious to know your experience with real estate taxes on south side. Did they go up a ton after you purchased?

Thank you!